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Bismuth(III) trifluoromethanesulfonate

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Synonym(s):
Bi(OTf)3, Bismuth tris(trifluoromethanesulfonate), Bismuth(III) triflate
Linear Formula:
Bi(OSO2CF3)3
CAS Number:
Molecular Weight:
656.19
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

core: bismuth
reagent type: catalyst

mp

>300 °C (lit.)

SMILES string

[Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Bi/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

Inchi Key

NYENCOMLZDQKNH-UHFFFAOYSA-K

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544132341010483311
vibrant-m

544132

Bismuth neodecanoate

vibrant-m

341010

Bismuth(III) iodide

vibrant-m

483311

Bismuth(III) phosphate

reaction suitability

core: bismuth, reagent type: catalyst

reaction suitability

core: bismuth, reagent type: catalyst

reaction suitability

core: bismuth, reagent type: catalyst

reaction suitability

core: bismuth, reagent type: catalyst

mp

>300 °C (lit.)

mp

-

mp

408 °C (lit.)

mp

>350 °C (lit.)

application

Bismuth(III) trifluoromethanesulfonate may be used as a catalyst in the following processes:
  • deprotection of acetals
  • cleavage of 2-tert-butoxy derivatives of thiophenes and furans
  • allylation of acetals to form homoallyl ethers
It may also be used as a substitute to corrosive triflic acid in Friedel-Crafts (FC) acylation and sulfonylation of arenes.
Catalyzes direct substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carbamates, and carboxamides.

Packaging

Bismuth(III) trifluoromethanesulfonate is an eco-friendly Lewis acid that can be prepared by reacting triflic acid with bismuth(III) trifluoroacetate.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Bismuth (III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes.
Repichet S, et al.
The Journal of Organic Chemistry, 64, 6479-6482 (1999)
Applications of bismuth (III) compounds in organic synthesis.
Leonard NM, et al.
Tetrahedron, 58(42), 8373-8397 (2002)
Bismuth (III) triflate in organic synthesis.
Gaspard-Iloughmane H and Le Roux C.
European Journal of Organic Chemistry, 2004(12), 2517-2532 (2004)
Maria Ricciardi et al.
ChemSusChem, 10(10), 2291-2300 (2017-04-05)
The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.
Hongbo Qin et al.
Angewandte Chemie (International ed. in English), 46(3), 409-413 (2006-12-06)

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